diff --git a/tests/functional/codegen/types/numbers/test_exponents.py b/tests/functional/codegen/types/numbers/test_exponents.py
index 702cbcb1dd..28dba59edc 100644
--- a/tests/functional/codegen/types/numbers/test_exponents.py
+++ b/tests/functional/codegen/types/numbers/test_exponents.py
@@ -173,3 +173,17 @@ def foo(b: int128) -> int128:
     c.foo(max_power)
     with tx_failed():
         c.foo(max_power + 1)
+
+
+valid_list = [
+    """
+@external
+def foo() -> uint256:
+    return (10**18)**2
+    """
+]
+
+
+@pytest.mark.parametrize("good_code", valid_list)
+def test_exponent_success(good_code):
+    assert compile_code(good_code) is not None
diff --git a/tests/unit/compiler/test_source_map.py b/tests/unit/compiler/test_source_map.py
index d99b546403..ae1999a26e 100644
--- a/tests/unit/compiler/test_source_map.py
+++ b/tests/unit/compiler/test_source_map.py
@@ -97,8 +97,44 @@ def update_foo():
     self.foo += 1
     """
     error_map = compile_code(code, output_formats=["source_map"])["source_map"]["error_map"]
-    assert "safeadd" in list(error_map.values())
-    assert "fallback function" in list(error_map.values())
+    assert "safeadd" in error_map.values()
+    assert "fallback function" in error_map.values()
+
+
+def test_error_map_with_user_error():
+    code = """
+@external
+def foo():
+    raise "some error"
+    """
+    error_map = compile_code(code, output_formats=["source_map"])["source_map"]["error_map"]
+    assert "user revert with reason" in error_map.values()
+
+
+def test_error_map_with_user_error2():
+    code = """
+@external
+def foo(i: uint256):
+    a: DynArray[uint256, 10] = [1]
+    a[i % 10] = 2
+    """
+    error_map = compile_code(code, output_formats=["source_map"])["source_map"]["error_map"]
+    assert "safemod" in error_map.values()
+
+
+def test_error_map_not_overriding_errors():
+    code = """
+@external
+def foo(i: uint256):
+    raise self.bar(5%i)
+
+@pure
+def bar(i: uint256) -> String[32]:
+    return "foo foo"
+    """
+    error_map = compile_code(code, output_formats=["source_map"])["source_map"]["error_map"]
+    assert "user revert with reason" in error_map.values()
+    assert "safemod" in error_map.values()
 
 
 def test_compress_source_map():
diff --git a/vyper/codegen/ir_node.py b/vyper/codegen/ir_node.py
index ff721fafcb..81ec47f10f 100644
--- a/vyper/codegen/ir_node.py
+++ b/vyper/codegen/ir_node.py
@@ -378,13 +378,18 @@ def is_complex_ir(self):
             and self.value.lower() not in do_not_cache
         )
 
-    # set an error message and push down into all children.
-    # useful for overriding an error message generated by a helper
-    # function with a more specific error message.
+    # set an error message and push down to its children that don't have error_msg set
     def set_error_msg(self, error_msg: str) -> None:
+        if self.error_msg is not None:
+            raise CompilerPanic(f"{self.value} already has error message {self.error_msg}")
+        self._set_error_msg(error_msg)
+
+    def _set_error_msg(self, error_msg: str) -> None:
+        if self.error_msg is not None:
+            return
         self.error_msg = error_msg
         for arg in self.args:
-            arg.set_error_msg(error_msg)
+            arg._set_error_msg(error_msg)
 
     # get the unique symbols contained in this node, which provides
     # sanity check invariants for the optimizer.
@@ -627,7 +632,7 @@ def from_list(
         else:
             return cls(
                 obj[0],
-                [cls.from_list(o, ast_source=ast_source) for o in obj[1:]],
+                [cls.from_list(o, ast_source=ast_source, error_msg=error_msg) for o in obj[1:]],
                 typ,
                 location=location,
                 annotation=annotation,
diff --git a/vyper/semantics/analysis/utils.py b/vyper/semantics/analysis/utils.py
index a31ce7acc1..8727f3750d 100644
--- a/vyper/semantics/analysis/utils.py
+++ b/vyper/semantics/analysis/utils.py
@@ -41,7 +41,7 @@ def _validate_op(node, types_list, validation_fn_name):
         try:
             _validate_fn(node)
             ret.append(type_)
-        except InvalidOperation as e:
+        except (InvalidOperation, OverflowException) as e:
             err_list.append(e)
 
     if ret:
diff --git a/vyper/semantics/types/primitives.py b/vyper/semantics/types/primitives.py
index 5c0362e662..dcc4fe8c8e 100644
--- a/vyper/semantics/types/primitives.py
+++ b/vyper/semantics/types/primitives.py
@@ -173,11 +173,11 @@ def _get_lr():
             if isinstance(left, vy_ast.Int):
                 if left.value >= 2**value_bits:
                     raise OverflowException(
-                        "Base is too large, calculation will always overflow", left
+                        f"Base is too large for {self}, calculation will always overflow", left
                     )
                 elif left.value < -(2**value_bits):
                     raise OverflowException(
-                        "Base is too small, calculation will always underflow", left
+                        f"Base is too small for {self}, calculation will always underflow", left
                     )
             elif isinstance(right, vy_ast.Int):
                 if right.value < 0: